1,5-(4-Dichloro­phen­yl)-3-(2,5-dimethoxy­phen­yl)pentane-1,5-dione

The crystal packing of the title compound, C₂₅H₂₂Cl₂O₄, is stabilized by inter­molecular C—H...Cl and C—H...O inter­actions, and also by C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.051
• wR factor = 0.120
• Data-to-parameter ratio = 22.6

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.688     0.921
            Tmin(prime) and Tmax expected:      0.863     0.921
            RR(prime) =      0.797
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.80

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: H.K. Fun and I.A. Razak are supervisors of Jeannie B.-J. Teh whereas S.M. Dharmaprakash is the supervisor of P.S. Patil and Balakrishna Kalluraya in this collaborative pulication. Mangalore University is involved in the extraction and synthesis of the title compound and USM is involved in the structure determination. All parties are involved in writing up the manuscript.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

1,5-(4-Dichlorophenyl)-3-(2,5-dimethoxyphenyl)pentane-1,5-dione

Crystal data

C25H22Cl2O4	F(000) = 952
Mr = 457.33	Dx = 1.398 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5632 reflections
a = 23.4679 (8) Å	θ = 2.5–30.1°
b = 5.6373 (2) Å	µ = 0.33 mm^−1
c = 16.5149 (5) Å	T = 100 K
β = 96.104 (2)°	Block, yellow
V = 2172.46 (13) Å^3	0.44 × 0.26 × 0.25 mm
Z = 4

Data collection

Brucker SMART APEX2 CCD area-detector diffractometer	6368 independent reflections
Radiation source: fine-focus sealed tube	4444 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 8.33 pixels mm^-1	θmax = 30.1°, θmin = 2.5°
ω scans	h = −33→29
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −7→7
Tmin = 0.688, Tmax = 0.921	l = −23→21
17945 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0498P)^2 + 1.0313P] where P = (Fo^2 + 2Fc^2)/3
6368 reflections	(Δ/σ)max < 0.001
282 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.535129 (18)	0.13690 (8)	0.37036 (3)	0.02271 (11)
Cl2	−0.06985 (2)	1.03452 (11)	0.33895 (5)	0.04964 (19)
O1	0.33355 (5)	0.9629 (2)	0.39470 (7)	0.0234 (3)
O2	0.19103 (6)	1.3261 (2)	0.51038 (9)	0.0281 (3)
O3	0.33272 (5)	1.2510 (2)	0.64602 (7)	0.0238 (3)
O4	0.18008 (6)	0.6291 (3)	0.76616 (8)	0.0275 (3)
C1	0.42556 (8)	0.6789 (4)	0.36251 (11)	0.0221 (4)
H1A	0.4183	0.8157	0.3317	0.027*
C2	0.46977 (7)	0.5308 (4)	0.34601 (11)	0.0213 (4)
H2A	0.4924	0.5676	0.3048	0.026*
C3	0.47990 (7)	0.3268 (3)	0.39185 (10)	0.0188 (4)
C4	0.44730 (8)	0.2694 (3)	0.45403 (11)	0.0206 (4)
H4A	0.4547	0.1317	0.4843	0.025*
C5	0.40328 (7)	0.4207 (3)	0.47054 (11)	0.0202 (4)
H5A	0.3813	0.3845	0.5126	0.024*
C6	0.39157 (7)	0.6261 (3)	0.42483 (10)	0.0174 (3)
C7	0.34506 (7)	0.7967 (3)	0.44051 (10)	0.0181 (4)
C8	0.31507 (7)	0.7621 (3)	0.51653 (10)	0.0187 (4)
H8A	0.3438	0.7528	0.5632	0.022*
H8B	0.2949	0.6116	0.5124	0.022*
C9	0.27235 (7)	0.9579 (3)	0.53198 (10)	0.0174 (4)
H9A	0.2899	1.1108	0.5210	0.021*
C10	0.21687 (7)	0.9341 (3)	0.47467 (10)	0.0185 (4)
H10A	0.2265	0.9230	0.4191	0.022*
H10B	0.1980	0.7875	0.4871	0.022*
C11	0.17557 (7)	1.1367 (3)	0.48015 (10)	0.0197 (4)
C12	0.11458 (7)	1.1033 (3)	0.44513 (11)	0.0206 (4)
C13	0.07488 (9)	1.2800 (4)	0.45717 (14)	0.0330 (5)
H13A	0.0866	1.4139	0.4873	0.040*
C14	0.01816 (9)	1.2592 (4)	0.42490 (15)	0.0389 (6)
H14A	−0.0082	1.3773	0.4337	0.047*
C15	0.00122 (8)	1.0612 (4)	0.37963 (14)	0.0320 (5)
C16	0.03955 (8)	0.8844 (4)	0.36558 (13)	0.0302 (5)
H16A	0.0277	0.7533	0.3340	0.036*
C17	0.09627 (8)	0.9052 (4)	0.39940 (12)	0.0256 (4)
H17A	0.1222	0.7851	0.3913	0.031*
C18	0.26221 (7)	0.9530 (3)	0.62172 (10)	0.0170 (3)
C19	0.29287 (7)	1.1054 (3)	0.67708 (10)	0.0183 (4)
C20	0.28315 (8)	1.1049 (3)	0.75925 (10)	0.0212 (4)
H20A	0.3027	1.2104	0.7955	0.025*
C21	0.24429 (8)	0.9465 (3)	0.78612 (10)	0.0210 (4)
H21A	0.2371	0.9484	0.8404	0.025*
C22	0.21599 (7)	0.7850 (3)	0.73277 (11)	0.0199 (4)
C23	0.22455 (7)	0.7906 (3)	0.65037 (10)	0.0192 (4)
H23A	0.2049	0.6848	0.6144	0.023*
C24	0.36322 (8)	1.4097 (4)	0.70231 (11)	0.0264 (4)
H24A	0.3905	1.4979	0.6751	0.040*
H24B	0.3829	1.3208	0.7463	0.040*
H24C	0.3367	1.5174	0.7234	0.040*
C25	0.15426 (8)	0.4457 (4)	0.71485 (12)	0.0271 (4)
H25A	0.1334	0.3403	0.7465	0.041*
H25B	0.1835	0.3587	0.6913	0.041*
H25C	0.1285	0.5151	0.6723	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0234 (2)	0.0223 (2)	0.0237 (2)	0.00050 (18)	0.00839 (16)	0.0001 (2)
Cl2	0.0238 (2)	0.0369 (3)	0.0845 (5)	−0.0007 (2)	−0.0117 (3)	−0.0026 (3)
O1	0.0266 (6)	0.0241 (7)	0.0201 (6)	0.0014 (6)	0.0050 (5)	0.0062 (6)
O2	0.0286 (7)	0.0185 (7)	0.0358 (8)	0.0008 (6)	−0.0029 (6)	−0.0053 (6)
O3	0.0277 (7)	0.0255 (7)	0.0182 (6)	−0.0130 (6)	0.0028 (5)	−0.0005 (6)
O4	0.0323 (7)	0.0287 (8)	0.0225 (6)	−0.0132 (6)	0.0078 (5)	0.0003 (6)
C1	0.0246 (8)	0.0236 (10)	0.0184 (8)	−0.0003 (8)	0.0036 (7)	0.0076 (8)
C2	0.0224 (8)	0.0258 (10)	0.0166 (8)	−0.0007 (8)	0.0062 (7)	0.0035 (8)
C3	0.0190 (8)	0.0202 (9)	0.0172 (8)	−0.0017 (7)	0.0021 (6)	−0.0035 (8)
C4	0.0248 (9)	0.0186 (9)	0.0190 (8)	−0.0007 (7)	0.0048 (7)	0.0037 (8)
C5	0.0216 (8)	0.0212 (10)	0.0187 (8)	−0.0022 (7)	0.0064 (7)	0.0023 (8)
C6	0.0183 (7)	0.0188 (9)	0.0148 (7)	−0.0019 (7)	0.0004 (6)	−0.0003 (8)
C7	0.0180 (8)	0.0211 (9)	0.0149 (8)	−0.0027 (7)	0.0006 (6)	−0.0005 (8)
C8	0.0193 (8)	0.0206 (9)	0.0163 (8)	−0.0003 (7)	0.0020 (6)	0.0012 (8)
C9	0.0206 (8)	0.0175 (9)	0.0142 (8)	−0.0022 (7)	0.0026 (6)	−0.0001 (7)
C10	0.0207 (8)	0.0177 (9)	0.0171 (8)	−0.0005 (7)	0.0015 (6)	−0.0029 (7)
C11	0.0228 (8)	0.0186 (9)	0.0176 (8)	−0.0007 (7)	0.0016 (6)	0.0000 (8)
C12	0.0213 (8)	0.0191 (9)	0.0216 (9)	−0.0010 (7)	0.0027 (7)	0.0008 (8)
C13	0.0269 (10)	0.0239 (11)	0.0467 (13)	0.0025 (9)	−0.0029 (9)	−0.0102 (10)
C14	0.0261 (10)	0.0284 (12)	0.0612 (15)	0.0074 (9)	0.0007 (10)	−0.0085 (12)
C15	0.0208 (9)	0.0282 (11)	0.0458 (12)	−0.0009 (8)	−0.0025 (8)	0.0012 (11)
C16	0.0270 (9)	0.0260 (11)	0.0366 (11)	−0.0047 (9)	−0.0008 (8)	−0.0078 (10)
C17	0.0232 (9)	0.0251 (11)	0.0291 (10)	0.0011 (8)	0.0052 (7)	−0.0052 (9)
C18	0.0197 (8)	0.0161 (9)	0.0155 (8)	0.0014 (7)	0.0027 (6)	0.0014 (7)
C19	0.0206 (8)	0.0163 (9)	0.0182 (8)	−0.0020 (7)	0.0028 (6)	0.0022 (7)
C20	0.0262 (9)	0.0209 (10)	0.0161 (8)	−0.0035 (8)	−0.0003 (7)	−0.0011 (8)
C21	0.0256 (8)	0.0228 (10)	0.0149 (8)	0.0000 (8)	0.0041 (7)	0.0020 (8)
C22	0.0206 (8)	0.0190 (9)	0.0204 (8)	−0.0017 (7)	0.0041 (7)	0.0053 (8)
C23	0.0206 (8)	0.0191 (9)	0.0177 (8)	−0.0024 (7)	0.0019 (6)	−0.0014 (8)
C24	0.0287 (9)	0.0268 (11)	0.0224 (9)	−0.0121 (8)	−0.0028 (7)	0.0016 (9)
C25	0.0295 (10)	0.0219 (10)	0.0304 (10)	−0.0083 (8)	0.0051 (8)	0.0010 (9)

Geometric parameters (Å, º)

Cl1—C3	1.7462 (18)	C10—H10B	0.9700
Cl2—C15	1.737 (2)	C11—C12	1.497 (2)
O1—C7	1.216 (2)	C12—C17	1.390 (3)
O2—C11	1.218 (2)	C12—C13	1.392 (3)
O3—C19	1.383 (2)	C13—C14	1.385 (3)
O3—C24	1.427 (2)	C13—H13A	0.9300
O4—C22	1.373 (2)	C14—C15	1.378 (3)
O4—C25	1.430 (2)	C14—H14A	0.9300
C1—C2	1.381 (3)	C15—C16	1.378 (3)
C1—C6	1.399 (2)	C16—C17	1.393 (3)
C1—H1A	0.9300	C16—H16A	0.9300
C2—C3	1.383 (3)	C17—H17A	0.9300
C2—H2A	0.9300	C18—C23	1.390 (2)
C3—C4	1.383 (2)	C18—C19	1.397 (2)
C4—C5	1.389 (3)	C19—C20	1.400 (2)
C4—H4A	0.9300	C20—C21	1.383 (3)
C5—C6	1.394 (3)	C20—H20A	0.9300
C5—H5A	0.9300	C21—C22	1.386 (3)
C6—C7	1.498 (2)	C21—H21A	0.9300
C7—C8	1.516 (2)	C22—C23	1.397 (2)
C8—C9	1.531 (2)	C23—H23A	0.9300
C8—H8A	0.9700	C24—H24A	0.9600
C8—H8B	0.9700	C24—H24B	0.9600
C9—C18	1.526 (2)	C24—H24C	0.9600
C9—C10	1.532 (2)	C25—H25A	0.9600
C9—H9A	0.9800	C25—H25B	0.9600
C10—C11	1.507 (2)	C25—H25C	0.9600
C10—H10A	0.9700
C19—O3—C24	116.27 (13)	C13—C12—C11	118.78 (17)
C22—O4—C25	117.67 (14)	C14—C13—C12	121.0 (2)
C2—C1—C6	121.04 (17)	C14—C13—H13A	119.5
C2—C1—H1A	119.5	C12—C13—H13A	119.5
C6—C1—H1A	119.5	C15—C14—C13	119.2 (2)
C1—C2—C3	118.90 (16)	C15—C14—H14A	120.4
C1—C2—H2A	120.5	C13—C14—H14A	120.4
C3—C2—H2A	120.5	C14—C15—C16	121.39 (18)
C4—C3—C2	121.63 (17)	C14—C15—Cl2	119.31 (16)
C4—C3—Cl1	119.27 (15)	C16—C15—Cl2	119.30 (17)
C2—C3—Cl1	119.10 (13)	C15—C16—C17	118.99 (19)
C3—C4—C5	118.95 (17)	C15—C16—H16A	120.5
C3—C4—H4A	120.5	C17—C16—H16A	120.5
C5—C4—H4A	120.5	C12—C17—C16	120.84 (18)
C4—C5—C6	120.79 (16)	C12—C17—H17A	119.6
C4—C5—H5A	119.6	C16—C17—H17A	119.6
C6—C5—H5A	119.6	C23—C18—C19	118.95 (15)
C5—C6—C1	118.67 (16)	C23—C18—C9	120.88 (16)
C5—C6—C7	123.03 (15)	C19—C18—C9	120.11 (15)
C1—C6—C7	118.28 (16)	O3—C19—C18	116.34 (14)
O1—C7—C6	120.31 (15)	O3—C19—C20	123.17 (16)
O1—C7—C8	121.49 (16)	C18—C19—C20	120.49 (16)
C6—C7—C8	118.14 (15)	C21—C20—C19	119.57 (17)
C7—C8—C9	114.53 (15)	C21—C20—H20A	120.2
C7—C8—H8A	108.6	C19—C20—H20A	120.2
C9—C8—H8A	108.6	C20—C21—C22	120.52 (16)
C7—C8—H8B	108.6	C20—C21—H21A	119.7
C9—C8—H8B	108.6	C22—C21—H21A	119.7
H8A—C8—H8B	107.6	O4—C22—C21	115.98 (15)
C18—C9—C8	108.73 (14)	O4—C22—C23	124.31 (17)
C18—C9—C10	112.85 (14)	C21—C22—C23	119.70 (16)
C8—C9—C10	111.25 (14)	C18—C23—C22	120.61 (17)
C18—C9—H9A	107.9	C18—C23—H23A	119.7
C8—C9—H9A	107.9	C22—C23—H23A	119.7
C10—C9—H9A	107.9	O3—C24—H24A	109.5
C11—C10—C9	113.96 (15)	O3—C24—H24B	109.5
C11—C10—H10A	108.8	H24A—C24—H24B	109.5
C9—C10—H10A	108.8	O3—C24—H24C	109.5
C11—C10—H10B	108.8	H24A—C24—H24C	109.5
C9—C10—H10B	108.8	H24B—C24—H24C	109.5
H10A—C10—H10B	107.7	O4—C25—H25A	109.5
O2—C11—C12	119.97 (17)	O4—C25—H25B	109.5
O2—C11—C10	121.59 (16)	H25A—C25—H25B	109.5
C12—C11—C10	118.42 (16)	O4—C25—H25C	109.5
C17—C12—C13	118.63 (17)	H25A—C25—H25C	109.5
C17—C12—C11	122.57 (17)	H25B—C25—H25C	109.5
C6—C1—C2—C3	0.5 (3)	C13—C14—C15—C16	−0.3 (4)
C1—C2—C3—C4	−0.7 (3)	C13—C14—C15—Cl2	−179.93 (19)
C1—C2—C3—Cl1	179.16 (14)	C14—C15—C16—C17	1.3 (3)
C2—C3—C4—C5	0.1 (3)	Cl2—C15—C16—C17	−179.03 (16)
Cl1—C3—C4—C5	−179.71 (14)	C13—C12—C17—C16	0.6 (3)
C3—C4—C5—C6	0.6 (3)	C11—C12—C17—C16	−177.84 (18)
C4—C5—C6—C1	−0.8 (3)	C15—C16—C17—C12	−1.5 (3)
C4—C5—C6—C7	−179.36 (16)	C8—C9—C18—C23	−80.7 (2)
C2—C1—C6—C5	0.2 (3)	C10—C9—C18—C23	43.2 (2)
C2—C1—C6—C7	178.87 (16)	C8—C9—C18—C19	96.35 (19)
C5—C6—C7—O1	−173.95 (17)	C10—C9—C18—C19	−139.72 (17)
C1—C6—C7—O1	7.5 (3)	C24—O3—C19—C18	178.85 (16)
C5—C6—C7—C8	8.8 (2)	C24—O3—C19—C20	−1.8 (3)
C1—C6—C7—C8	−169.77 (16)	C23—C18—C19—O3	175.43 (16)
O1—C7—C8—C9	−2.9 (2)	C9—C18—C19—O3	−1.7 (2)
C6—C7—C8—C9	174.31 (15)	C23—C18—C19—C20	−4.0 (3)
C7—C8—C9—C18	−159.60 (14)	C9—C18—C19—C20	178.91 (17)
C7—C8—C9—C10	75.52 (19)	O3—C19—C20—C21	−177.19 (17)
C18—C9—C10—C11	64.0 (2)	C18—C19—C20—C21	2.2 (3)
C8—C9—C10—C11	−173.51 (14)	C19—C20—C21—C22	1.5 (3)
C9—C10—C11—O2	18.1 (2)	C25—O4—C22—C21	−174.30 (17)
C9—C10—C11—C12	−163.60 (15)	C25—O4—C22—C23	6.5 (3)
O2—C11—C12—C17	170.30 (18)	C20—C21—C22—O4	177.40 (17)
C10—C11—C12—C17	−8.0 (3)	C20—C21—C22—C23	−3.4 (3)
O2—C11—C12—C13	−8.2 (3)	C19—C18—C23—C22	2.1 (3)
C10—C11—C12—C13	173.53 (18)	C9—C18—C23—C22	179.19 (17)
C17—C12—C13—C14	0.4 (3)	O4—C22—C23—C18	−179.32 (17)
C11—C12—C13—C14	179.0 (2)	C21—C22—C23—C18	1.5 (3)
C12—C13—C14—C15	−0.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···Cl1^i	0.93	2.83	3.684 (2)	154
C9—H9A···O3	0.98	2.34	2.778 (2)	106
C10—H10A···O1	0.97	2.60	3.168 (2)	118
C20—H20A···O1^ii	0.93	2.52	3.432 (2)	167
C25—H25B···Cg^iii	0.96	2.84	3.669 (2)	145

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, −y+5/2, z+1/2; (iii) x, y−1, z.